Phase-transfer and other types of catalysis with cyclopropenium ions
Abstract This work establishes the cyclopropenium ion as a viable platform for efficient phase-transfer catalysis of a diverse range of organic transformations. The amenability of these catalysts to large-scale synthesis and structural modification is demonstrated. Evaluation of the molecular structure of an optimal catalyst reveals some unique structural features of these systems. Finally, a discussion of electronic charge distribution underscores an important consideration for catalyst design. Aromatic ions: Tris(dialkylamino)cyclopropenium ions are shown to be effective carbocationic phase-transfer catalysts for a variety of mainstay transformations. The cyclopropenium platform is shown to be modular and accessible on scale. An X-ray structure and electron-density map revealed some unique features of this architecture (see scheme).
Bandar, Jeffrey S.,Tanaset, Anont,Lambert, Tristan H.
Kinetic Resolution of Neopentylic Secondary Alcohols by Cu-H-Catalyzed Enantioselective Silylation with Hydrosilanes
A nonenzymatic kinetic resolution of sterically congested alcohols having a quaternary carbon atom in the β-position is reported. The catalyst system CuCl/NaOtBu/(R,R)-Ph-BPE together with a 3,5-xylyl-substituted tertiary hydrosilane enable enantioselective silylation of the hydroxy group. Several alcohols are obtained with good to excellent selectivity factors, and there are no other known straightforward methods to access these motifs.
Oestreich, Martin,Papadopulu, Zaneta
supporting information
p. 438 - 441
(2021/01/13)
On the π-π interaction in the benzylation of ketones
The benzylation of a set of nine ketones provides enough information to establish how the ketone structure affects the existence of a π-π interaction. The presence of a phenyl moiety starting from the a-carbon atom and flexibility in cyclic ketones are st
Diez-Barra, Enrique,Merino, Sonia,Sanchez-Verdu, Prado,Torres, Jose
p. 11437 - 11448
(2007/10/03)
Novel Rearrangement and Cyclization Processes Resulting from Bromination of 1,1-Dibenzyltetralin Derivatives
Addition of bromine to hydrocarbon 1 results in an aromatic alkylation to form the bicyclononane derivative 5.Addition of bromine to ketone 3 in acetonitrile solution results in a dienone-phenol rearrangement to form phenol 6, while reaction of ket
Miller, Bernard,Shi, Xiaolian
p. 1677 - 1681
(2007/10/02)
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